James "Buster" Douglas is best known for his stunning upset of Mike Tyson on February 11, 1990, in Tokyo to win the undisputed heavyweight title. At the time Tyson was undefeated and considered to be the best boxer in the world, as well as one of the most feared heavyweight champions in history due to his domination of the division over the previous three years. The only casino to make odds for the fight (all others declining to do so as they considered the fight such a foregone conclusion) had Douglas as a 42-to-1 underdog for the fight, making his victory, in commentator Jim Lampley's words, "The biggest upset in the history of heavyweight championship fights." Douglas held the title for eight months and two weeks, losing on October 25, 1990, to Evander Holyfield via third-round knockout, in his only title defense.

This Everlast boxing glove was signed in black by Douglas and inscribed, "Tyson KO 2/11/90." This item includes a JSA sticker and COA.